The instant invention provides novel nor-methyl jasmonate having the structure: ##STR3## and optical isomers thereof having the structures: ##STR4## as well the novel intermediates for producing same having the structure: ##STR5## and optical isomers thereof having the structures: ##STR6## which are also useful in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles; as well as processes for preparing same according to the reaction sequence: ##STR7## and organoleptic uses of said nor-methyl jasmonate and nitriles for augmenting or enhancing the fresh, clean, jasmine, floral aroma of perfume compositions, colognes and perfumed articles.
Chemical compounds which can provide "fresh, clean" jasmine aromas and which can round out jasmine perfumes and colognes and perfumed articles having jasmine aromas are desirable in the art of perfumery and in the art of detergent manufacture and fabric softener manufacture. Many of the natural materials which provide the jasmine fragrance and contribute such desired nuances to perfumery compositions are high in cost, e.g., jasmine absolute; they are unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will aid in replacing, enhancing or augmenting the essential fragrance notes provided by natural jasmine oil or jasmine absolute. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree or else contribute undesirable or unwanted odor to the compositions. The search for materials which can provide a more refined jasmine aroma has been difficult and relatively costly in the areas of both natural products and synthetic products.
Methyl jasmonate having the structure: ##STR8## has an important use in the aroma in perfume compositions and perfumed articles of jasmine absolute. The absolute configuration of methyl jasmonate was published in Tetrahedron, 1965, Vol. 21, pages 1501 to 1507.
Alkyl-2-alkyl-3-oxacyclopentan carboxylates are described for use for their floral and woody aroma nuances in perfumes in British Pat. No. 1,353,898. These compounds have the generic structure: ##STR9## wherein R represents branched or straight chain alkyl or cycloalkyl having from 4 up to 8 carbon atoms and R' represents methyl or ethyl. These compounds are indicated to be prepared using the compound having the structure: ##STR10## as a starting material, reacting it with HCN or a HCN precursor to form the compound having the structure: ##STR11## and then reacting that compound with an alcohol in the presence of an acid catalyst. The reaction sequence set forth in British Patent Specification 1,353,898 is as follows: ##STR12##
French Pat. No. 7,326,210 issued on Feb. 14, 1975 discloses a genus of compounds including the compound having the structure: ##STR13## and indicates that this genus is useful in perfumery but does not specifically disclose the compound having the structure: ##STR14## for use in perfumery. In any event, the compounds having the structures: ##STR15## have unexpected, unobvious and advantageous properties when compared to the compound having the structure: ##STR16##
Furthermore, nothing in the prior art, however, in either British Pat. No. 1,353,898 or in any other prior art discloses the compound having the structure: ##STR17## or its stereoisomers or intermediates for preparing same having the structure: ##STR18## or processes for preparing such compounds according to the reaction sequence: ##STR19##
The compound having the structure: ##STR20## and the stereoisomers thereof have properties unexpected, unobvious and advantageous in perfumery and in perfumed articles with respect to compounds having the generic structure: ##STR21## wherein R and R' are defined as above or methyl jasmonate itself having the structure: ##STR22##